Iwould like to express my appreciation to the many people and institutions who assisted me in researching and writing this book: Michael Carroll and Shannon Whibbs of Dundurn; Edward (Ted) and Jane Cobean and the Brocton Heritage Committee; Monica Graham; A.E. Dalton; Peter Edwards; the Colorado Historical Society; the Metropolitan Toronto Reference Library; the Rooms of St. John’s, Newfoundland and Labrador; the Ontario Provincial Archives; the Alberta Provincial Archives; Pinkerton’s Inc.; the Walkerton Public Library; Library and Archives Canada; Mary Moriarty, Damien Rodden, Kingston Penitentiary Museum; and as always the staff of the Guelph Public Library.

Introduction

Livingon the wrong side of the law has never been an enviable existence. Those who have experienced it have often been among the first to warn juvenile offenders against falling into the trap of lawlessness — advice that they themselves failed to heed in their youth. Life on the run can certainly have moments of adrenaline-pumping excitement, but one can get the same thing from any number of legitimate challenges, from bungee-jumping to working as a professional in search-and-rescue operations.

There is nothing glamorous about being a fugitive from the law, no matter how much Hollywood romanticizes it. The highly successful organized-crime boss with a fine house and an offshore account full of tainted money is in many ways no different from the two-bit burglar who resides in cheap rooms and lives from one robbery to the next. Both live in fear of making a mistake, of being betrayed, or of any unforeseen clue that will bring the police to their door.

Of course, there is always the threat of punishment. In colonial Canada that could mean flogging, imprisonment, or being hanged and then having your body gibbeted as a warning to others. Over the years the more barbaric punishments were discarded as unfit for a civilized and enlightened nation. It was also obvious that they were ineffective as deterrents to crime.

Some people who live on the wrong side of the law are drawn by the prospect of “easy money.” Like career criminal Micky McArthur, they might think that working is for fools. Or, like the outlaw Newton brothers, they might have seen how years of honest toil got their families and neighbours nowhere, and decided that armed robbery would be an acceptable method not only of survival, but also of financial success. As the Newtons put it, robbery was their “business.” Such criminals don’t fear punishment because they don’t expect to get caught. They believe they are smart enough to always stay one jump ahead of the police.

Other people, like Sydney Lass, wander over to the wrong side of the law while they are still very young and never find their way back. Lass spent more time in prison than he did out of it and never learned to be anything but a thief. For Lass and many others like him, jail becomes an occupational hazard — part of the game. Harsh sentences meted out only to only punish do nothing to help them change their ways. If anything, they turn out criminals who are only more bitter and all the more seasoned in the cynicism of underworld life. Short-sighted “get tough” policies of populist “law and order” governments fill jails, but history has shown that they don’t do a thing to address the social problems that are at the root of crime.

This doesn’t mean that the criminal is absolved of all responsibility. No matter how dire an individual’s circumstances, it still comes down to a matter of choices. Verne Sankey could have pursued an honest career as an engineer for the CPR. He chose the wrong side of the law and became a bootlegger, bank robber, and kidnapper. The Newton boys in the 1920s, and Micky McArthur in the 1970s said that they only wanted money and didn’t intend to hurt anybody. “We wasn’t thugs,” said Willis Newton. But the Newtons didn’t hesitate to shoot bank messengers during a holdup in downtown Toronto. McArthur was responsible for the shooting of four police officers. When a person uses a weapon to commit robbery, that person is a thug, whether or not physical harm is done to other people. The potential for extreme violence is always at hand, and tragedy can be but a heartbeat away, for those who live on the wrong side of the law.

Chapter 1

Newfoundland Desperadoes:

A Rogues’ Gallery

Therecorded history of the province of Newfoundland and Labrador is the oldest of any part of Canada, predating even the earliest documented use of the wordCanada. Lawlessness on the island of Newfoundland began early in the seventeenth century, when it was a base for pirates like Peter Easton and Henry Mainwaring. Later, the interior became a haven for the outlawed Masterless Men, escaped indentured servants and Royal Navy deserters who sought freedom in the wild.

Throughout their long colonial period, Newfoundlanders were subject to the same harsh laws as the common people of Britain. In the earliest years, the usual punishment for theft was hanging. It didn’t matter if the culprit had stolen a few shillings or a cow. In time, the number of crimes punishable by death was reduced, but penalties were still severe. They included whipping, branding with a hot iron, banishment, and the confiscation of property.

In 1777, for example, Lawrence Hallohan was hanged for forging a bill for eight pounds. That same year, Lawrence Dalton followed him to the gallows for forging bills for twenty shillings and seventeen shillings. However, when Patrick Knowlan was convicted of stealing an item valued at ten pence, he wasn’t sentenced to hang. Instead, he had a halter put around his neck and was dragged to whipping posts set up at various locations in St. John’s where he was given a total of sixty lashes on his back by the “common whipper.” He forfeited all of his goods and property, was obliged to pay the court costs, and then was banished from the colony forever. If he returned to Newfoundland, he would be imprisoned and subjected to sixty lashes every Monday until passage on a ship could be found for him.

Offences such as public drunkenness, disorderly conduct, or sticking your tongue out at your employer could result in lashes or a day locked in the stocks, where you were an object of ridicule and the target for all the manure and other filth passersby wanted to throw at you. Most of the individuals subjected to these harsh punishments could hardly be considered hardened criminals. The existence of such measures is far more telling of the legal system that applied them than of the unfortunates who received them. Nonetheless, old time Newfoundland did have its share of ne’er-do-wells who were willing to risk everything for personal gain, and so slipped over to the wrong side of the law.

Downing and Malone

In 1832, Patrick Downing and Patrick Malone were working on the farm of Robert Crocker Bray at Harbour Grace. As they bent their backs to raising stumps with crowbars, Malone allegedly told Downing that following the recent fire that had destroyed much of Harbour Grace, he had carried a bag into Bray’s house. That bag, he said, had been buried to protect it from the fire because it contained money. Forty or fifty pounds! That was more money than either of them had ever seen. Malone said he slept in a room next to the one in which Bray kept the money bag, and that stealing it would be easy. Downing had no qualms about robbing Bray, but he thought the job would require four men. He wanted to bring his two brothers in on it. Malone said he didn’t trust them, and the matter was dropped for the time being.

The following spring, Malone went out on the ice for the annual seal hunt. That was a hazardous way to earn a few shillings and it had Malone thinking once again about the money in Bray’s house. He plotted with Downing, and they came up with a scheme that involved not just robbery, but murder. Malone said he had enlisted the Bray’s housemaid, Ellen Coombs, as an accomplice by promising to marry her.

One night in July 1833, Downing and Malone went into the Bray house. They killed Robert in the kitchen with two blows of a tomahawk. Mrs. Bray was out of town, but little Samuel Bray and Ellen Coombs were in an upstairs bedroom. Whether the housemaid was really involved in the plot would never be known, because she and the child were both hacked to death.

The murderers ransacked the house, but found no bag of money. They took whatever cash and valuables they could find; a total value between thirty and forty shillings. Then they started a fire in an upstairs bedroom and another one at the foot of the stairs before leaving the house.

Downing and Malone slipped off to Bear’s Cove, a little over a mile away, to hide their loot. They were certain that all evidence of the crime would be consumed by the flames. On their way back they met some men who told them the Bray house was on fire. They joined in spreading the alarm.

To the killers’ dismay, neighbours had gone into the house and put out the fires before the building could be engulfed. The butchered bodies had been found. Suspicion immediately fell on Malone, since he had been living in the house.

The Harbour Grace Magistrate, a doctor named Stirling, told Malone that if he confessed, he wouldn’t hang. In a signed statement, Malone placed the blame on Downing. He said that he had been sitting in the Bray house, rocking little Samuel, when Downing burst in and committed the murders. He admitted that he had helped hide the loot and disclosed the location. Downing was arrested, and both men were bound over for the next assize. Of course, Downing gave a different version of the crime, saying that Malone had done the killing.

The trial was held in St. John’s on January 3, 1834, and lasted nine hours. The presiding judge, Henry John Boulton, wouldn’t allow Malone’s statement to be read to the jury because it had been made after Malone had been told it would save his life. The accused men blamed each other. Boulton told the jury, “I believe the confessions of the two culprits were fully much of the same tenor and character, only that each charged the other with being the actual murderer. They differed only as to which one did the bloody deed.”

Amazingly, the judge also told the jury to disregard anything Downing had said against Malone, as he believed the evidence against Malone was very slight. It took the jury less than an hour to reach a verdict of “guilty” for both men. Downing was condemned to death, but to the astonishment of all, Malone was sentenced to life in prison. “His life may be spared,” Boulton said. “He will never again be allowed to infest society with his presence.”

At that time there was no process of appeal. Two days after the trial, Patrick Downing was publicly hanged on a scaffold set up on Market House Hill. According to the local press, he showed “the most astonishing composure and fortitude.” The reporter also noted that, “The execution was witnessed by an immense concourse of people, who behaved in the most decorous and orderly manner.”

By the standards of the time, the Bray murders had been judiciously avenged. But there were some who felt that justice hadn’t been served. They believed that Malone had done the killing, and then made a spurious “confession” to save his own life. By court order, Downing’s body was cut down and taken to Harbour Grace, the scene of the crime. There it was gibbeted — hung in chains — as a warning to would-be lawbreakers.

Some of Downing’s friends held Dr. Stirling responsible for a miscarriage of justice because he had illegally obtained Malone’s confession with a promise of clemency. One night, Downing’s decomposing corpse was cut down from the gibbet by persons unknown and the chains were removed. Dr. Stirling found the grisly remains on his doorstep the next morning. There was an accompanying note: “Dr. S. This is your man you were the cause of bringing him here take and bury him or Lookout should you be the cause of allowing him to be put up again we will mark you for it so Do your duty and put him out of sight. truly A friend from Carbonear. [sic]”

Dr. Stirling heeded the warning. He had the body placed in a coffin and buried in the yard of the Harbour Grace courthouse. It was never determined who really struck the blows that killed the three victims.

John Flood

Colonial Newfoundland was better known for pirates than highwaymen, but at least one Newfoundlander who lived on the wrong side of the law met his demise because of highway robbery. Today we associate the termhighwaymanwith images of flamboyant mounted robbers like England’s Dick Turpin, romantically portrayed in verse and fiction as dashing “knights of the road.” In fact most of them — including Turpin — were thugs, and they were as likely to be on foot as on horseback. Any petty holdup of a traveller on a public road was classified as highway robbery.

Because of missing documents, little is known of Newfoundland highwayman John Flood. Sometime in 1834, he robbed the stagecoach that ran between St. John’s and Portugal Cove, an important port for passenger vessels that served communities in Conception Bay. Flood stopped the coach on the Portugal Cove Road, in the vicinity of Kent’s Pond. It isn’t known if he called out the famous highwayman command, “Stand and deliver!”

Flood was soon arrested. On December 9, 1834, he was tried for robbery and assault, convicted, and sentenced to death. No documentation survives to confirm that the sentence was carried out. However, evidence indicates that a man who was hanged on January 12, 1835, was John Flood. The highwayman (if it was indeed he) was the last person to be publicly executed in Newfoundland.

Brady and Naughton

In January 1842, a pair of British criminals named Thomas Brady and William Naughton looted the Manchester branch of the Bank of England of nineteen thousand pounds — well over a hundred thousand dollars in today’s currency. While Scotland Yard detectives searched for them the length and breadth of Great Britain, the bandits were enjoying a luxurious Atlantic crossing on the steamerBritannia, the most famous passenger ship of the day. One of their fellow passengers was Charles Dickens. Brady and Naughton would later claim that they shared Dickens’s company at meals and took strolls around the deck with him. The truth of that is questionable, since Dickens was seasick for almost the entire voyage.

When the ship reached New York, Brady and Naughton were confident that they were beyond the long arm of British law. However, they soon learned from the newspapers that back home the police had discovered their identities and their means of escape. If they were found in New York, they’d be arrested and put on the first ship back to England.

Brady and Naughton went to the New York docks in search of a ship that would take them to any place they thought the police wouldn’t be likely to look for them. They found a vessel that was bound for Fogo, Newfoundland. Rather than pay for passage and leave a money trail, they signed aboard as deck hands.

At Fogo, Brady and Naughton helped unload the cargo. After being paid off, they took a schooner to St. John’s. Now they felt they had given Scotland Yard the slip. The colonial capital wasn’t New York, but it was still a place where a pair of crooks with a lot of money could enjoy themselves.

The bank robbers passed themselves off as debonair, well-educated gentlemen of means named Thomas Bradshaw and William O’Kelly. They were soon the toast of the small, elite social circle of St. John’s, and were invited to dine in the best homes. When they astounded listeners with the news that they had crossed the ocean with Charles Dickens, people pumped them with questions about the great man and about the fate of Little Nell, the heroine of the serialized novel,The Old Curiosity Shop.

Things were going well enough for the pair until they ran out of small currency and had to dip into the swag from the bank. They went into the Dublin Bookstore and asked the proprietor, Bernard Duffy, if he could change a one-hundred-pound note. Duffy was astonished to see a bill of such large denomination — and suspicious. He told them he didn’t have that much money on the premises. They agreed to leave the note with him, and come back after supper when he’d had time to gather up some cash.

As soon as they were gone, Duffy took the note to Bishop Michael Fleming, who sent him to the manager of the British Bank of North America. The manager had recently received some newspapers from England, and he recalled reading about the Manchester bank robbery. He sorted through the papers and found the article. It included a list of serial numbers of the stolen notes. The bill “Bradshaw and O’Kelly” had given Duffy had one of those numbers. The manager immediately alerted the chief of police. The robbers were arrested in their room at Johnson’s Hotel, where the constables also found the loot.

News of the arrest swept through St. John’s. When the high society people heard it, they were shocked; not because their new friends had been exposed as criminals and imposters, but because they thought the police had made an incredible blunder. Several of them went to the jail on Signal Hill to vouch for the two and protest such undignified treatment of gentlemen.

A few days after the arrest, Brady and Naughton appeared in court for a preliminary hearing. They had hired a lawyer, John Little, who argued that a newspaper article was hardly strong enough evidence to keep them in jail. W.B. Rowe, Q.C., representing the Crown, countered that possession of a large amount of money that had been identified as stolen was indeed good enough reason for them to be held in custody, especially since they could not satisfactorily explain how they came to be travelling with such an incredible sum of money. The court ruled that the pair remain in jail until arrangements could be made to send them back to England. The editor of the St. John’sTimescommented:

We are not, technically speaking, learned in the law; but we may be allowed to observe, that with the strong circumstantial evidence there is of their guilt, in addition to what is determined as newspaper information, their immediate release would not only defeat the ends of justice, but go for the encouragement of delinquency in others.

According to one story, a friend smuggled files to the prisoners in a cake. Whether or not that’s true, Brady and Naughton did manage to get out of their cell one foggy night and make a run for it. Naughton tripped and fell and a guard shot him in the leg. Brady kept running down the hill until he reached Maggoty Cove. He dove into the water and swam across the Narrows. He then made his way to a squatter community in the Southside Hills and vanished from documented history.